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Mar Drugs
2012 Nov 05;1011:2467-80. doi: 10.3390/md10112467.
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Isolation and structure elucidation of GM4-type gangliosides from the Okinawan starfish Protoreaster nodosus.
Pan K
,
Tanaka C
,
Inagaki M
,
Higuchi R
,
Miyamoto T
.
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Three new ganglioside molecular species, termed PNG-1, PNG-2A, and PNG-2B were isolated from pyloric caeca of the starfish Protoreaster nodosus. Their structures were elucidated using a combination of spectroscopic and chemical methods, and characterized as 1-O-[8-O-methyl-N-acetyl-α-neuraminosyl-(2→3)-β-galactopyranosyl]-ceramide for PNG-1, 1-O-[β-galactofuranosyl-(1→3)-α-galactopyranosyl-(1→4)-8-O-methyl-N-acetyl-α-neuraminosyl-(2→3)-β-galactopyranosyl]-ceramide for PNG-2A, and 1-O-[β-galacto furanosyl-(1→3)-α-galactopyranosyl-(1→9)-N-acetyl-α-neuraminosyl-(2→3)-β-galactopyr anosyl]-ceramide for PNG-2B. PNG-2A and PNG-2B represent the first GM4 elongation products in nature.
Figure 1. (a) Protoreaster nodosus and (b) Pyloric caeca of P. nodosus.
Figure 2. Negative ion FAB-MS spectra of PNG-1 (A), PNG-2A (B) and PNG-2B (C) and their major fragment ion peaks due to cleavage of the glycosidic linkages.
Figure 3. The core structures of Gangliosides (GLSs) from P. nodosus. (a) PNC-1 and (b) PNG-1.
Figure 4. Partial HMBC spectrum and key HMBC and nOe correlations of PNG-1.
Figure 5. The core structure of PNG-2A and key nOe correlations.
Figure 6. EI-MS spectrum of the acetate of partially methylated NeuAc derived from 9-linked Neu5Ac and the assignment of its valuable fragment ion peaks.
Figure 7. The core structure of PNG-2B and key nOe correlations.
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